Graphical Abstract: Eur. J. Org. Chem. 14/2005

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  • Papers available ahead of print in Early View at www.interscience.wiley.com

    Issue 14/2005

    Pages 28513142

    COVER PICTURE

    The cover picture shows the X-ray crystal structures of thecompounds obtained by the alkylation of a conjugated por-phyrinogen precursor at its macrocyclic nitrogen atoms with2-(methylenenaphthyl) groups. The presence of the N-alkylgroups introduces intermolecular stacking interactionswhich culminate in a 1-dimensional stacked array for thefully N-substituted derivative. The N-alkylation enhances theability of the compounds to form anion radical and cationradical species and permits tuning of the electrochemicalproperties of the core porphyrinogen. Details are discussedin the article by J. P. Hill et al. on p. 2893ff.

    MICROREVIEW Contents

    G. Bartoli, M. Bartolacci, A. Giuliani,2867E. Marcantoni,* M. Massaccesi

    Diastereoselective Lewis Acid Mediated Re-ductions of -Alkyl--Functionalized CarbonylCompounds

    Keywords: Carbonyl compounds / Chelates / Dia-stereoselectivity / Lewis acids / Reduction

    Eur. J. Org. Chem. 2005, 28552862 www.eurjoc.org 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 2855

  • SHORT COMMUNICATIONS

    L. D. Field, B. A. Messerle,* S. L. Rumble2881

    Iridium(I)-Catalysed Tandem Hydrosilylation-Protodesilylation of Imines

    Keywords: Hydrosilylation / Imines / Iridium / Solventeffects / Homogeneous catalysis

    M. Yoshimatsu,* M. Kawamoto, K. Gotoh2884

    First Lewis Acid Catalyzed Generation andReaction of -Organylsulfanyl and -Organyl-selanyl Carbenium Ions Using Ethyl -Fluoro-acetate Derivatives

    Keywords: CC coupling / Carbocations / Scandium /Catalysis / Lewis acids / Fluorinated com-pounds

    G. Zoppellaro,* M. Baumgarten2888

    One-Step Synthesis of Symmetrically Substi-tuted 2,6-Bis(pyrazol-1-yl)pyridine Systems

    Keywords: Nitrogen heterocycles / Halogenation /Grignard reaction / Synthesis design

    FULL PAPERS

    J. P. Hill,* W. Schmitt, A. L. McCarty,2893K. Ariga, F. DSouza*

    Structures, Spectral and Electrochemical Pro-perties of N-(Naphth-2-ylmethyl)-AppendedPorphyrinogens

    Keywords: Porphyrinogen / Redox chemistry /Spectroelectrochemistry / Puckered macro-cycles / Quinones

    P. Daz Perez, M. I. Garca-Moreno,2903C. Ortiz Mellet, J. M. Garca Fernandez*

    Synthesis and Comparative Glycosidase Inhibi-tory Properties of Reducing CastanospermineAnalogues

    Keywords: Carbamates / Castanospermine / Inhibi-tors / Thiocarbamates / Indolizidines /Enzymes

    2856 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim www.eurjoc.org Eur. J. Org. Chem. 2005, 28552862

  • J. O. Subbotina,* W. M. F. Fabian,*2914E. V. Tarasov, N. N. Volkova, V. A. Bakulev

    Synthetic and Theoretical Aspects of NewDimroth Rearrangement of 6-Aminopyran-2-ones to 6-Hydroxypyridin-2-ones via Carb-amoyl Ketenes

    Keywords: Rearrangement / Reaction mechanisms /Hydrogen bond / Ketene intermediates /DFT calculations

    L. A. Wozniak, M. Gora,2924M. Bukowiecka-Matusiak, S. Mourgues,G. Pratviel, B. Meunier, W. J. Stec*

    The P-Stereocontrolled Synthesis of PO/PS-Chimeric Oligonucleotides by Incorporation ofDinucleoside Phosphorothioates Bearing anO-4-Nitrophenyl Phosphorothioate ProtectingGroup

    Keywords: Antisense agents / Nucleosides / Oligo-nucleotides / Stereochemistry

    H. Abe, M. Takase, Y. Doi, S. Matsumoto,2931M. Furusyo, M. Inouye*

    Tautomeric Self-Dimerization and MolecularRecognition Properties of 2-AminopyrimidinoneDerivatives as Triple Hydrogen-Bonding Mod-ules in Molecular Assemblies

    Keywords: Molecular recognition / Self-assembly / Nu-cleobases / Hydrogen bonds / Tautomerism

    B. M. P. Verbist, W. M. De Borggraeve,*2941S. Toppet, F. Compernolle, G. J. Hoornaert

    Development of New Amino(oxo)piperidine-carboxylate Scaffolds and Their Evaluation as-Turn Mimics

    Keywords: Intramolecular DielsAlder reaction /2(1H)-pyrazinones / -Turn mimic

    Eur. J. Org. Chem. 2005, 28552862 www.eurjoc.org 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 2857

  • A. S. Abreu, P. M. T. Ferreira,2951M.-J. R. P. Queiroz,* I. C. F. R. Ferreira,R. C. Calhelha, L. M. Estevinho

    Synthesis of -Benzo[b]thienyldehydrophenyl-alanine Derivatives by One-Pot Palladium-Cata-lyzed Borylation and Suzuki Coupling (BSC)and Metal-Assisted Intramolecular Cyclization Studies of Fluorescence and AntimicrobialActivity

    Keywords: Dehydrophenylalanines / Benzothiophenes /Borylation / Suzuki coupling / Cyclization /Indoles / Fluorescence / Antimicrobialactivity

    K. Marino, C. Marino, C. Lima, L. Baldoni,2958R. M. de Lederkremer*

    The First Chemical Synthesis of UDP[6-3H]--D-galactofuranose

    Keywords: Carbohydrates / Galactofuranosyltrans-ferase / Isotopic labeling / Nucleotides /UDP-Galf

    S. A. A. El Bialy, H. Braun, L. F. Tietze*2965

    Enantioselective Synthesis of -Alkylmalates asthe Pharmacophoric Group of Several NaturalAlkaloids and Glycosides

    Keywords: Alkaloids / Antitumor agents / Dioxolan-ones / Enantioselective synthesis / Furans /Glycosides / Malates

    D. G. A. Pinto, A. M. S. Silva,* C. M. Brito,2973A. Sandulache, J. R. Carrillo, P. Prieto,A. Daz-Ortiz, A. de la Hoz,*J. A. S. Cavaleiro

    Reactivity of 3-Styrylchromones as Dienes inDielsAlder Reactions under MicrowaveIrradiation: A New Synthesis of Xanthones

    Keywords: 3-Styrylchromones / Microwave irradia-tion / Xanthone-type compounds / Cyclo-addition / Solvent-free reactions / Abinitio calculations

    2858 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim www.eurjoc.org Eur. J. Org. Chem. 2005, 28552862

  • M. C. Schopohl, A. Faust, D. Mirk,2987R. Frhlich, O. Kataeva, S. R. Waldvogel*

    Synthesis of Rigid Receptors Based on Triphen-ylene Ketals

    Keywords: Receptors / Supramolecular chemistry /Synthetic methods / Oxidative couplingreaction / Triphenylene ketals

    M. Schelper, O. Buisine, S. Kozhushkov,3000C. Aubert*, A. de Meijere,* M. Malacria*

    Cobalt(I)-Mediated Intramolecular [222]Cocyclizations of (Methylenecyclopropyl)diynesas an Easy Access to Cyclopropanated Oligo-cycles

    Keywords: Cyclopropanes / Enediynes / Cobalt / Cycli-zation / Metal template synthesis

    M. Kordes, M. Brands, M. Es-Sayed,3008A. de Meijere*

    Preparation of Cyclopropane Analogues of theNatural Antibiotic TAN 1057 A/B

    Keywords: Amino acids / Antibiotics / Cyclopro-panation

    J. Reuber, R. Frhlich, D. Hoppe*3017

    Asymmetric -Deprotonation and SubstitutionReactions of (Z)-1,3-Diphenyl-1-propenyl N,N-Diisopropylcarbamate

    Keywords: Asymmetric synthesis / Carbanions / Allyliccompounds / Homoaldol addition / ()-Sparteine

    M. Hocek,* R. Pohl, I. Csarova3026

    Highly Methylated Purines and Purinium Saltsas Analogues of Heteromines

    Keywords: Purines / Natural products / Cross-coupling / Alkylation / 15N NMR spec-troscopy

    Eur. J. Org. Chem. 2005, 28552862 www.eurjoc.org 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 2859

  • A. Isidro-Llobet, J. Guasch-Camell,3031M. Alvarez, F. Albericio*

    p-Nitrobenzyloxycarbonyl (pNZ) as a Tempor-ary N-Protecting Group in Orthogonal Solid-Phase Peptide Synthesis Avoiding Diketo-piperazine and Aspartimide Formation

    Keywords: Amino protecting group / Nitro reduction /SnCl2 reduction / PNZ group in SPPS /Combinatorial chemistry / Side reactions

    G. A. Kraus,* N. Zhang, J. Q. Wei,3040J. H. Jensen*

    Regiochemical Control by Remote Substituents A Selective Synthesis of Angularly FusedRing Systems

    Keywords: DielsAlder / Quinones / Regiocontrol /Regioselectivity

    M. Alvaro, C. Aprile, H. Garca,* E. Peris3045

    A Soluble and Reusable Colorimetric SensorBased on the Covalent Attachment of a Triaryl-pentenedione to Poly(ethylene glycol)

    Keywords: Sensors / Polymers / Heterocycles / Cycliza-tion / Colorimetry

    P. Astolfi,* M. Panagiotaki, L. Greci3052

    New Insights into the Reactivity of Nitrogen Di-oxide with Substituted Phenols: A Solvent Effect

    Keywords: Substituted phenols / Nitrogen dioxide /Hydrogen transfer / Electron transfer /Solvent effects

    D. Biondini, L. Brinchi, R. Germani,3060L. Goracci, G. Savelli*

    Dehydrogenation of Amines to Nitriles inAqueous Micelles

    Keywords: Amines / Oxidation / Nickel / Nitrile /Micelles

    2860 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim www.eurjoc.org Eur. J. Org. Chem. 2005, 28552862

  • P. A. Troshin,* A. S. Peregudov,3064D. Mhlbacher, R. N. Lyubovskaya

    An Efficient [23] Cycloaddition Approach tothe Synthesis of Pyridyl-Appended FullereneLigands

    Keywords: Azomethine ylides / Cycloaddition /Fullerenes / N ligands / Picolylamines

    A. Pastor,* W. Adam, T. Wirth, G. Toth3075

    Diastereoselective Reactions of the Tiglic AcidFunctionality Mediated by Oxazolidine ChiralAuxiliaries: A Mechanistic Comparison ofDMD and m-CPBA Epoxidations versus SingletOxygen and PTAD Ene Reactions

    Keywords: Ene reaction / Epoxidation / Hydrogenbonding / Singlet oxygen / Stereochemistry

    M. Roussel, T. Benvegnu,* V. Lognone,3085H. Le Deit, I. Soutrel, I. Laurent,D. Plusquellec

    Synthesis and Physico-Chemical Properties ofNovel Biocompatible Alkyl d-Mannopyranosid-uronate Surfactants Derived from Alginate

    Keywords: Alginate / Bioorganic chemistry / Mann-uronic acid / Micelles / Surfactants

    P. Kirsch,* A. Hahn3095

    Liquid Crystals Based on Hypervalent SulfurFluorides: Exploring the Steric Effects of ortho-Fluorine Substituents

    Keywords: Density functional calculations / Fluorin-ation / Liquid crystals / Hypervalent sulfurfluorides / Mesogens / Molecular modelling

    M. A. L. Podeschwa, O. Plettenburg,3101H.-J. Altenbach*

    Flexible Stereo- and Regioselective Synthesis ofmyo-Inositol Phosphates (Part 1): Via Symmetri-cal Conduritol B